


take more cord and bind me faster yet

by libraralien



Category: Black Sails
Genre: Anal Fingering, F/M, Finger Sucking, First Time, Masturbation, Pre-Series
Language: English
Status: Completed
Published: 2017-08-30
Updated: 2017-08-30
Packaged: 2018-12-21 15:13:33
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,560
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11946921
Author URL: https://archiveofourown.org/users/libraralien/pseuds/libraralien
Summary: One version of how Jack and Anne's first(ish) time might have gone.





	take more cord and bind me faster yet

Jack had the morning to himself, which was a rare occurrence. They had recently arrived to Nassau with a prize, rather unfortunately, at the same time as half the ships that could call Nassau their home. As such, the entire island was swamped with people and everything seemed to be moving at a molasses pace, as everybody jostled for space and food and services. They had been in Nassau for days and were only just getting a chance to distribute shares of their prize to the crew. 

Normally Jack would have gone to assist with the keeping of records, being the only one of the three of them who had learned to read and write as a child, and thus was the quickest and most skilled at it. But with the delays, he had gotten all the record books squared away days ago.

Anne had gone to help Charles with the distribution instead. Supposedly, her job was to stand there and look surly as his backup, should any man be in the mood to start a fight. Of course, Charles was plenty menacing on his own, and really Anne being there was a reminder to the men of her closeness to the captain and his trust in her, to give all the crew a chance to see her sitting next to him when they collected their shares, and to see her without Jack, lest they think Jack was the only one who had Charles's ear. 

Some of the newer men had been getting bold when it came to discussing Anne and their opinions about a woman being on the ship, so it was necessary to refresh their memories as to the respect she demanded on the ship.

Jack knew how it looked. Or rather, he knew how people looked at the two of them. The effete intellectual, some would say a dandy, and the tough brutish woman; what a pair they made. Jack always had an ear out for what people said about Anne, and by extension, himself.

"I heard Vane allows a woman on his ship, and that she shares a bed with his quartermaster." (True)

"I heard they are secretly married." (False)

"I heard she has the parts of both a man and a woman in her trousers, that's why Vane allows her on the ship. (False)

"I heard she was a feral child when they brought her on." (Partially true)

"I heard Rackham's completely subservient to her. She says the word and he comes running like a dog." (No comment)

Nothing threatening necessarily, but enough to warrant a good strong glare for every member of the crew from both Anne and Charles sitting shoulder-to-shoulder.

He was alone, with nothing to do, in a brothel of all places.

One of the other side effects of the glut of people on the island at the moment was that the beaches were crowded with tents and the inns in town completely full. Ever since he became quartermaster, Jack had insisted on renting a room while in Nassau. He didn't rise in rank to continue sleeping in a tent on the sand. With the inn's full, the local brothels had started renting out rooms, he was sure with the hope that they would pay for a girl while they were there. 

So now Jack was staying in some whore's bedroom, while she piled into a friend's room somewhere else in the building, he was sure. It felt strange and rather personal, as many of her belongings were still in the room, though nothing valuable, Jack thought. The upside of this was that not only did Jack have free time, but also he had a bathtub at his disposal. 

He prided himself on a certain degree of personal upkeep, beyond that of the average pirate. Even at sea, he shaved every day. Even so, he didn't often have both the time and means to thoroughly get clean, to really get all the salt and scum out from his hair and skin. So he called for fresh water and spent the morning using some whore's good soap washing every inch of himself, as the sun streamed in through the window. 

But even he could only stretch a bath so long once clean. After he got out, he idly walked around the room while toweling off, still with nothing to do with his time. He noticed the room had a rather nice vanity, so he took the opportunity to neaten up his facial hair. Once finished, he poked around through the items sitting on the vanity; various make-ups and powders and perfumes. He picked up one bottle and sniffed it, assuming it would be another bottle of some scented something or other, but smelled nothing other than the slight smell of some variety of plain oil. Useful for a whore, he supposed. He regarded himself in the mirror and figured it would not hurt to steal a bit, just for his skin. The constant salt really did dry out one's body. 

The oil was warm slightly from sitting in the sun and felt pleasant as he rubbed it over his whole body. He regarded his now gleaming naked figure in the mirror. Never one to lack ego, he decided he was maintaining himself rather well. He was tan and muscled, not as tan and muscled as Charles perhaps, but then again, who was? He ran a hand over his torso, then turned to get a look at his backside, as he ran one hand down a slick thigh, feeling his own muscle under his hand. As he gazed at his reflection, he concentrated for a moment on the ambient sounds of the brothel around him; mostly people walking and talking, but distant moans and rhythmic pounding. He felt a twinge of arousal

For the first time since being there, he thought that it was rather a pity he was in a brothel and wasn't getting fucked. He considered the possibility for a moment, but as of late there had been...something between himself and Anne.

As it was, people had assumed they were fucking for years. Their first several years together Anne was but a child, and people had assumed they were siblings, and now people assumed they were married, and thus, fucking. Jack didn't blame them, they certainly behaved like a married couple. 

And now? Now they still weren't fucking. But also, it seemed, neither were they not fucking. At his estimate, there had now been a couple dozen instances of passionate kissing, all instigated by Anne, all in the middle of the night, with no discussion before or answer. The last few times had escalated to rather desperate dry humping and the two of them grabbing each other over their clothes, during which Jack had come in his trousers. 

Jack had no idea what any of it meant, but saw no point in bringing it up; he had long ago learned that Anne would either discuss something or she wouldn't and there was no use in trying to force anything out of her. He was also worried that if he brought it up it would break the spell and these instances would cease, and well, he was rather enjoying them.

The whole situation might have seemed strange to an outsider, but he thing was, it had been years since there was any modesty between the two of them. They had shared quarters for years, so they would happily bathe or change clothing in front of one another without a second thought. They had both tended the other's body when wounded in a fight or otherwise. 

They had seen each other's bodies at their lowest point; once Jack had lanced blisters on the inside of Anne's thighs after a particularly stormy trip had rendered her breeches more or less permanently damp for two solid weeks; once he drank some rancid water that poisoned him with a fever so severe he couldn't stand for three days and caused him to shit himself. Anne had pressed cool rags onto his overheated naked body and wordlessly cleaned him up. 

After passing through the depths of embarrassments such as those, admission of carnal desires seemed hardly a trifle. He had been careful when Anne was younger, but naturally after living together for so long, they had both walked in on one another in moments of solitary pleasure. Anne always gave him shit about it when she was the one walking in on him, but in a way that Jack could recognize as Anne being good natured. And being in cramped quarters in a shared bed for months on end, both were happy to pretend to be asleep while the other touched themself. 

So their recent development was new, but from Jack's perspective, it hardly felt sudden. And he certainly didn't want to disturb it, whatever it was.

This did not help his current situation, which was that he found he rather wanted to tumble into bed with somebody. He supposed that somebody would just have to be himself. He was not overly disappointed; lazing around nude with as much time as he wanted, freshly bathed and gleaming with oil was quite an upgrade from his usual furtive jerking off next to a sleeping, or politely pretending to be sleeping, Anne, into the nearest rag.

He lay down on top of the bed and took his already half hard cock in one hand, still rubbing his other over his body. He moved his hand on his cock slowly, trying not to rush the experience.

He closed his eyes and tried to summon the memory of Anne crawling on top of him in the middle of the night, mouth hungrily against his, pulling at his hair, hips thrusting against his through both of their clothing. He wanted more. He wanted her here, on top of him again, shoving into his mouth, the weight of her body on his, pressing him into the bed. He could feel himself growing harder and harder, as he sped up his hand.

At the time he had felt so overwhelmed by Anne, he couldn't have imagined any further act. He wanted that overwhelming feeling again. He imagined sticking his head between her legs, pressing his face into her so deeply he couldn't see or smell anything else, her thighs clamping on his head until there is nothing in his world but Anne. He moaned, thrusting up into his own hand. 

The feeling of wanting something more suddenly crystallized into a physical desire to have something up his ass. When else would he have such a good opportunity if not now? He shifted off the bed and stole the oil again off the vanity (he would tip extra for the room to make up for it). He lay back down with his legs propped up and apart and carefully rubbed more of it onto his hand and between his legs, taking care not to spill it on the bed spread. He closed his eyes and went back to jerking his cock, concentrating on relaxing. After a moment, he reached down with the hand that wasn't busy and pressed one finger into himself, causing him to gasp.

It was not an unfamiliar sensation, he was no virgin; there had been a time before Anne, and then a time when Anne was a child, and even when him and Anne had grown together so completely it no longer felt right to go to bed with others, there had been times when piracy wasn't lucrative and money had to be made for himself and Anne one way or another. But it had been a while. He had forgotten how much he had liked the feeling.

As he carefully pressed further into himself, as if connected be some hidden mechanics, his cock throbbed in his hand. He was uncomfortably hard, and the desire to simply thrust furiously at himself and orgasm immediately was powerful, but he tried to hold off. He moved his finger slowly and carefully, trying to be delicate with himself. Even with his gentle movements, he was so sensitive, the feeling was immense. After some effort, he managed to push a second finger in as well. He let his mind wander to Anne again, imagined her sprawled out between his legs, lazily fingering him and jerking him off.

Suddenly his fantasy of Anne was interrupted by a very real and very angry Anne throwing the door open, and immediately furiously slamming it behind her. She glared directly at him and seemed not surprised to have caught him like this, but angry that he dare do such a thing while she was in a bad mood.

"What the fuck, Jack?"

"I thought you weren't supposed to be back for hours," he said, pulling his knees together to grant himself some degree of modesty, trapping one arm between his thighs. He covered his cock with one hand, pressing it into his belly. His other hand was still partially inside himself, causing it to conveniently cover the rest of his undercarriage.

"Got in a fight with Charles."

"Oh, good. Over what?" he felt awkward and exposed, but was reluctant to remove his fingers from himself, having gone through the effort of getting them in. 

She let out a huff. "Before we took this prize, we knew it was dangerous, so we voted that anybody who got crippled would get a slightly bigger share. Well, Holloway comes up, and says, he should get the bigger share, he done lost three fingers. Charles says, losing a finger ain't crippling. I said, how's he supposed to fire a gun, then? So Charles said, he didn't lose them in battle, he lost them when they got caught in some poorly done rigging. I said, not his fault about the rigging, he deserves the bigger share."

"Was all this...in front of the men?"

"Yeah, all those that was lined up."

Jack sighed, "Oh so you questioned his authority in front of his men? Excellent work endearing yourself to Charles, honestly, I'm surprised he hasn't fallen in love with you yet."

"Fuck you, Jack."

"Yes, I really am trying to, dear, if I could just have a moment to."

"Well I need you to stop. You need to come back with me, side with me against Charles."

"I'm sorry dear, but I simply am not going to do that. I'm rather enjoying myself, and it's not worth getting into a fight with Charles over."

Jack closed his eyes and slowly began moving his hand on his cock again, as if to indicate that he was through with this conversation. He opened them again when he heard the sound of a chair being scraped against the floor. Anne had grabbed a chair from against the wall and placed it facing the foot of the bed, so that she was more or less looking straight up his arse. Without breaking eye contact with him, she sat firmly down and steeled her chin. So she was trying to make him uncomfortable? Well, two could play at that game.

He splayed his legs back out and looked her straight back in the eyes. He began slowly, luxuriously moving his fingers in and out of himself with one hand, stroking his cock loosely with the other. As he thrust into himself up to the knuckles, he knit his brow and let out his most whorish moan. He began to lift his hips slightly off the bed in order to thrust into his own hand, while giving Anne an even more spectacular view in the process. He was trying to make a point, but God, he really is completely open to her, she may as well be a midwife, the view she has, he thought. 

Her face was steely and resolute in response to his increased fervor.

He removed his hand from his cock, and let it wander over his thighs, chest, neck, across his mouth, other hand still thrusting slowly inside himself.

"Well now you are just being ridiculous," Anne said, a slight hitch in her voice. 

Jack raised his eyebrows in a kind of faux innocence. "Oh?"

"Going so slow like that. Just get it over with."

"Make me," he wanted to say, but resisted, out of the fear that Anne would indeed take him up on it and physically threaten him. Instead he let out another loud moan. 

Anne flushed furiously, mumbled, "Shut the fuck up," and then leaned up onto the bed and over him, pushing her mouth down onto his. If she was trying to arouse him so as to speed the whole affair along...it was working. 

He wrapped his hand back around his cock, involuntarily clenching on himself. Anne was propped up on her knees against the bed, not touching him anywhere but with her mouth on his. He so wanted to reach up and grab her hands and press them onto his body, anywhere, everywhere, but he resisted. He didn't want this ruin whatever it was between them. 

Something in his face or breath or body must have alerted Anne to his desire (he had not yet ruled out that she could read his mind), because he felt one of her hands against the inside of his thigh. Reading her mind back, he slowly pulled his fingers out of himself and grabbed her hand, pressing it against himself. He was fairly sure she had never done this before, but she did not hesitate, immediately pressing two fingers carefully into him. He was thankful he was oiled and loosed up enough that they went in with relative ease. Her fingers were smaller than his, but just as rough. 

She pushed into him, thrusting more aggressively than he had with himself. He pushed back, matching her rhythm, until by any account she was well and truly fucking him. 

Her mouth broke off his and he felt her shift her weight on the bed and he felt her eyes on his body again. He opened his to look at her, engrossed and powerful above him. His mouth hung open, never closed after being opened by her kiss. 

She reached up with her other hand and slid two of her fingers into his mouth. 

With fingers inside him at both ends, he felt utterly consumed by her now. She was leaning over him, face directly over his, her thick red hair falling on either side of his face, blocking out his vision until all there was in the world, all there was of him, was Anne. He felt as if he was being restrained to the bed, pushed down by the sheer presence of her will. 

He imagined himself strapped to the bed - like Odysseus lashed to his mast as he sailed past the sirens. He too felt as if her were going mad with desire, but unlike Odysseus, he never wanted to be released. He wanted her entirely, inside and out. He pushed his head up onto her fingers so that they hit the back of his throat, forcing him to gag, drool beginning to spill out of the corners of his mouth and tears formed at the corners of his eyes. 

He looked her straight in the eye, no longer combatively, but plaintively now, as if he was begging her for something. He bobbed his head on her fingers like one would a cock, lavishing them with his tongue. Her face too no longer looked like she was trying to win a fight, but had softened into a determined expression.

She pressed into him with both hands, causing him to at once to gag and to thrust his hips up desperately into his fist. Unable to hold back any longer, he came almost immediately. The indignities did not stop at his stamina. He whimpered in a distinctly undignified manner, biting down on Anne's knuckles on one hand, clenching around the other. 

In the sea of sensations, he registered that he was coming so hard, that some of his come had hit him on his own chin, to say nothing of the mess he made of his chest and belly. 

As he lay there panting, Anne gently removed both her hands from him and stood up off the bed, and he realized she was panting too, as if by entering him she too had felt some of what he had. 

He was utterly debauched before her. She was flushed, and her fury over Charles seemed to have dissipated, which was more or less a miracle when it came to Anne, so he knew she was not unaffected by the experience, but compared to him she looked miraculously dignified. She was clothed, standing, and looking imperious, having shed nought but her hat in the experience, while he was sprawled out on the bed, covered in his own sweat, his seed splattered on his belly, cheeks and chin coated in drool, and a line of tears coming out of each eye back toward the pillow. 

She quietly replaced her hat onto her head and walked over the the bathtub to rinse her hands and then walked back over to wipe them dry against the bed.

"Clean yourself up Jack, you look a mess," she said affectionately, before heading back out the door, off to win another battle.

**Author's Note:**

> Title from Thomas Hobbes's 1675 translation of the _The Odyssey,_


End file.
